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This is the first of a series of Virtual Book Club posts with lessons derived from Ryan Holiday’s book, The Obstacle is the Way. This book is a favorite of Fortune 500 CEO’s, NFL coaches and players, and comes recommended by college coaches like Alabama’s Nick Saban. This section is derived from the Introduction section of the book.

What if the big problem that you face today could actually be the springboard to your greatest success?

In The Obstacle is the Way, we learn that you can turn any problem into an advantage. But, only if you start thinking about your problem the right way. What you need is a system to reframe your problems.

A New Way of Thinking About Obstacles

Why is having a system of thinking about problems so important? Couldn’t we just focus on solving our current problems? After all, once they are solved, it’s clear sailing, right?

But, this doesn’t work. We tell ourselves things like this but the truth is that problems and obstacles will never go away. No matter how far we progress, how much we accomplish, or how much money we make, we will find and face new problems.

A brief look at human history illustrates this very well. Our ancestors faced far worse problems than we do today and solved them. If you’re reading this, you will probably never worry about having food to eat or a bed to sleep in. Or, if you’re a parent, you can reasonably expect all your children to live to see 18 years old. However, in the year 1800, 43.3% of children would die before their 5th birthday.

Even though humanity has come so far, we still face plenty of problems today – some old and some new. The reality of human existence is that problems are a part of it. It’s a reality of our physical world and our mental and emotional wiring.

So, since problems aren’t going away, we need a new framework for thinking about them. We must no longer shy away from them, sweep them under the rug, or live in denial.

We must find a way of thinking that will keep us calm, composed, and prepared to handle whatever may come. The place to begin is simply realizing this: your current problem contains an advantage specifically for you.

The Advantage Built In to Your Biggest Problems

Intel CEO Andy Grove once stated that: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” Holiday says that this quote is equally true of individuals:

All great men and women used their greatest challenges as the fuel to achieve their success.

This is not about “glass half full” platitudes. In Holiday’s words:

The point is not to be “positive” but to be ceaselessly creative and optimistic

Not: This is not so bad.

But: I can make this good.

Examples of Those Who Turned Weakness into Strength

Over 33% of all entrepreneurs are dyslexic, including billionaire Richard Branson. Dyslexia is almost twice as common in entrepreneurs as the general population.  Some estimates put the percentage of entrepreneurs with any learning disability as high as 50%. We will discuss in a later post in this series why learning disability may turn into a strength for some individuals.

Actor Arnold Schwarzenegger was rejected repeatedly during auditions and told that he could never be an American movie actor due to his accent. The accent has, of course, become the signature of one of the world’s most famous actors.

President Barack Obama turned both his own multi-racial background and the racial issues raised during his 2008 bid into a vision of hope, change, and a speech on race relations still considered to be one of the best in history. Arguably both Obama’s “disadvantages” ultimately made him more remarkable and fueled his meteoric rise to the White House.

President Donald Trump has been widely ridiculed and sometimes despised for the things he has said in his political career. But, this very criticism has only made him stronger with his base. Trump has leaned into the very things he has been criticized for rather than away from them. He turned a disadvantage into the source of his strength.


How do you get start turning your problem into your solution? It is a simple process, but, not an easy one. We will begin digging into specifics in Part II on Friday. Click here to join the JABBED Virtual Book Club mailing list so that you don’t miss any posts from this series.

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Want to skip ahead and read the full book now? Check out The Obstacle is the Way on Amazon using the link below.